Functionalized (meth)acrylamides are important class of specialty monomers. These types of monomers are considered the most reactive ones and their polymers and co-polymers have been used in both industrial and consumer products such as water-treatment, coating, oil fields, home and personal care products. Most of the functionalized (meth)acrylamides are produced by Ritter reactions from readily available acrylonitrile (for Ritter reactions: Organic Process Research & Development 1999, 3, 23{tilde over (2)}234 & K. L. Reddy Tetrahedron Letters 44 (2003) 1454 1453-1455).
U.S. Pat. No. 3,506,707 described acrylamidoalkanesulfonic acids prepared by a two step reaction sequence comprising first reacting an olefinic compound containing at least one allylic hydrogen atom with an acyl hydrogen sulfate to form a sulfonated intermediate, and subsequently reacting this intermediate with an acrylonitrile in the presence of sulfuric acid and then with water. U.S. Pat. No. 4,239,885 described a process for the preparation of diacetone acrylamide whereby acrylonitrile and diacetone alcohol are reacted in at least 93% sulfuric acid to form a novel intermediate reaction product which is recovered as a crystalline solid, washed with an organic solvent to remove colored oily impurities along with sulfuric acid, and hydrolyzed to produce diacetone acrylamide. U.S. Pat. No. 5,712,413 described a process for the preparation of N-hydrocarbyl-substituted amides such as tert-butylacrylamide via the Ritter reaction using solid heteropolyacid catalysts. DE 86-3644009 (1988) described N-Substituted acrylamides containing ester groups. GB 2103216 described a process for preparing N-alkylamides of acrylic acid or methacrylic acid, wherein acrylonitrile or methacrylonitrile is reacted with a compound having an optionally substituted alkyl group with 3 to 40 carbon atoms, capable of forming an alkyl carbonium ion under the effect of sulphuric acid.
There is a market need for reactive monomers bearing phosphonic acid and other relevant phosphorus functional groups. The polymer from these monomers will find various applications such as water treatment, rheology modifier, surface modification, etc.
U.S. Pat. No. 4,526,728 described a way to make 2-(meth)acrylamido-2-methylpropanephosphonic acid from isobutene, PCl5 and (meth)acrylonitrile. However, the yields were low and large amounts of hazardous wastes were generated from the process. There still are needs for reactive (meth)acrylamide monomers bearing phosphonate or phosphinate functional groups with an efficient process.